electrophilic addition reactions

hydrohalogenation

-h, -x

HCl, HBr, HI

C+

markovnikov

no stereospecificity

radical addition of hbr

-br, -h

HBr, ROOR, hv

radical

anti-markovnikov

no stereospecificity

acid-catalyzed hydration

-h, -oh

h20 w/ cat Hx, H2SO4, or H3O+

C+

markovnikov

no stereospecificity

halogenation

-x, -x

br2, cl2

x+

no regioselecivity

anti stereospecificity

halohydrin

-x, -oh

(br2, cl2) w/ h2O

x+

markovnikov-like regioselectivity

anti stereospecificity

oxymercuration demercuration

-h, -oh

1) Hg(OAc)2, H2O. 2) NaBH4

x+

markovnikov

anti stereospecificity

anti-dihydroxylation

-oh, -oh

1) mCPBA. 2) H3O+

x+

no regioselectivity

anti stereospecificity

hydroboration oxidation

-oh, -h

1) BH3, THF. 2) H2O2, NaOH

concerted

anti-markovnikov

syn stereospecificity

syn-dihydroxylation

-oh, -oh

1) KMnO4 or OsO4. 2) H2O

concerted

no regioselectivity

syn stereospecificity

ozonolysis

cleaves double bond and gives both carbons a carbonyl

1) O3. 2) SMe2

concerted

no regioselectivity

no stereospecificity

hydrogenation

-h, -h

H2 (g) and Pt, Ni, or Pd/C

concerted

no regioselectivity

syn stereospecificity